Wingmen
by TheTenggi
Summary: Henry "Hiccup" Haddock, the outcast, the useless and much more. He has no friends, his crush ignores him and his father doesn t care at all. After graduating from High school he has the choice: Join the family bussiness or take his own way to make his father proud of him. Modern AU, Rating might change to M in future chapters. (Sorry I suck at summarys).
1. Prologue part I

**Hey there. This is my first fanfic so please don´t flame if it´s bad. I want to know your opinion though. What do you think of the first chapter? Should I continue writing this story or not?**

**Disclaimer: I do not own How to train your dragon or any of th characters used in this chapter.**

**OoOoO**

_Hiccup_

It is another sunny day in Berk. The fifth in a row actually, which is quite uncommon for this region. So it is a thoroughly good day…well, it should have been. For most people in town it probably was. Not for me though. Who I am not to enjoy such a day? I´m Hiccup, well Henry but no one ever calls me that and the reason, why it is a bad day might surprise you… well, today is the day when I graduate from Berk high school. Now you are probably even more confused than before as to why I wouldn´t be happy about graduating but you have to know, I´m not exactly popular. In fact my only friend is Fishlegs, a bulky guy with blonde hair and a good heart. His actual name is Frederic, but for some mysterious reason he prefers to be called by his nickname.

So here I am, laying in my bed and thinking about the day to come. When my alarm clock finally went off, I forced myself out of the comfortable covers and stumbled over to my wardrobe.

As every other day, I take out a green T-shirt, a brown bear fur vest and a pair of worn jeans. I quickly get dressed and walk down the stairs into the kitchen. I look around a see a small piece of paper on the table. I picked it up and see it was a note from dad. To be honest, I don´t really know why he keeps writing these things. I got used to his absence long ago. Regardless of better judgment I read the note:

"_Good morning Hiccup,  
>I have to be at work early today, so don´t worry about me. I will probably be gone till late at night, so you don´t have to wait for me. Have fun at school today.<br>Dad"_

I sigh. He had obviously forgotten, what day it is and I am not going to remind him.

I get myself breakfast, and take my keys, before stepping out of the house and jumping into my car, a pitch black Chevrolet Camaro SS. I know, expensive car for a teenage boy, but my father has enough money to afford that. The bad thing is, that I don´t even like the car.

I pull out of the driveway and make my way to school, all the way thinking about, what I would do after high school.

**OoOoO**

_3 hours later – Berk High School – Normal Pov_

Hiccup waits behind the football stadium, together with all the other students that would graduate today. He is currently standing right next to Fishlegs, watching the others adjusting their gown or checking their hair style.

He sees his cousin Scott, or Snotlout, as his friends call him, walk by. He is a burly guy with dark hair and lots of muscles. Scott is the star quarterback of the school and as such one of the most popular students in Berk High.

As usual he completely ignores Hiccup and Fishlegs and heads over to a gorgeous girl with golden hair. Astrid Hofferson, the most popular and beautiful girl by far, is standing close by her friends, the twins Rache and Trevor Thuffnut.

Scott casually places his arm around her shoulder and starts to flirt with her. He couldn´t even end his first sentence, before Astrid punches him in the face and steps away from him.

Hiccup smirks at this. Although he has a huge crush on the girl and he knows, that she wouldn´t as much as look at him, he loves to see his cousin getting beat up by her, which occurs on an almost daily basis, because he feel satisfied to see, that the guy who bullied him the most over the last few years, got it back.

The girl is just about to yell at Scott for trying to flirt with her and calling her his babe again, as a teacher walks in and announces, that it is only as few minutes before the ceremony would start.

"This is it", Fishlegs says quietly beside him, as they form a row, to go out on the field. Hiccup says nothing and just gets to his place, to wait for the teacher to lead the into the stadium.

**OoOoO**

**Sooo… this is the first chapter of Wingmen. As I already said at the beginning, please tell me what you think of it. This is just an idea I had to get out of my head, and although I have a general idea of how the story will go on, I don´t really have any ideas for the next few chapters to come, so feel free to send me some of your ideas.  
>The next chapter will start the actual plot of the story and explain some more things this chapter didn´t (that is if you want me to continue this story)<br>Thank you for reading and feel free to PM me or review.**

**-TheTenggi**


	2. Prologue part II

**Hello I´m back and oh gosh! 10 Favorites and 13 Followers on the first day the first chapter is up?! Thank you all so much! I would have never thought, that the stuff I´ve uploaded is actually worth something.  
>But enough of that…Let´s get on with the story:<strong>

**OoOoO**

While he waits for the teacher to return, Hiccup looks around and reminisces all those times he had been in this stadium before…

_A much younger Hiccup is casually leaning against a wall at the side of the field, watching his cousin´s coach yell at the boys to hurry up with their exercise._

_When they are finished the coaches announces the date of their first match against a rivaling team. As all the others, Scott seems really excited about it and then hurries over to Hiccup._

"_Hey little cuz. We have an important match next week. You better make sure to be here, so that I can show you how to play this game!"_

_Hiccup just rolls his eyes at his cousin, as he has no interest in football at all. Or in any sport that is. Because of his scrawny build, he was never really good at anything athletic and he was never interested too. This was hard to accept for his father, who was the star quarterback when he was in High School. But over the years he got used to being disappointed in his son. Now he always takes Hiccup to watch football games in hope to rouse any sort of interest in sports. But Scott doesn´t understand his cousin´s despise of the game and still thinks, he could get him to do sports by showing him how good he is at it himself._

"_How often do I have to tell you not to call me 'little cuz'? I am not even a month younger than you!"_

"_You are still younger than me.", Scott smirks. "So what about the game? Are coming or not?"_

"_I guess I have no choice than to come…As soon as my Dad hears about it, he will drag me here anyway."_

_Just then a group of older players walks by. One of them sees Scott and me talking and calls over to him. "Hey Scott! What are doing there talking with this twig! You should not talk to him like that. It´s not good for your reputation. Certainly you don´t want to be on the same level as this little nerd here." _

_Scott looks at him in shock. His reputation is everything for him. He worked hard to the place where he is now, the youngest quarterback since four years. He looks back at Hiccup and the boy can see the uncertainty in his cousin´s eyes._

_Scott finally sighs and pushes Hiccup. He catches the boy off guard and he stumbles back and falls into the mud near the outline of the field._

"_No…I don´t", the bigger guy answers the other player. Without looking back he turns away from Hiccup and walks to the team´s lockers. _

Hiccup sighs as he remembers the day his cousin turned against him. Ever since that day Scott humiliated him at every occasion he got. Hiccup likes to think that that wouldn´t have happened if the other boy, who graduated the year after this incident, hadn´t mocked him, Scott would have never become what he is now. But he knew, even if this had never happened, Scott would have drawn the same conclusion sooner or later.

As the teacher finally comes back and tells them to go inside the stadium, Hiccup takes another look at the long line of students.

As an honor student he was in the first part of the row. The others were lined up alphabetically behind the honor students.

Right in front of him, he recognized the trademark braid of Astrid Hofferson coming out from under her cap. Behind him was Fishlegs with a tense expression on his face.

As they enter the stadium Hiccup can hear the school band play the standard graduation music. The parents, who were already sitting at their places were clapping loudly and Hiccup wondered if he would feel any better if he knew that his dad was one of them.

As they all sit down, the crowd slowly begins to calm down and as no one is clapping anymore, the principal stands up from his seat and begins with a long, tiring speech.

After what seemed like forever, he finally finishes and begins to call the names of the students.

Hiccups sits there patiently waiting for his name to be called, while he remembers how he had imagined his graduation a few years ago. He had always thought his dad would be there with him, along with all the parents of his friends and when his name would be called, his father would stand up and cheer for him, yelling how proud he was of his son.

Now, while he is sitting there in his uncomfortable folding chair, he realizes how wrong he was back then. His father isn´t there at all and if he would be, he certainly wouldn´t shout that he was proud of this failure that calls himself his son.

"Michael T. Gregory" the principal calls out and Michael stands up to take his diploma and shake the principal´s hand. Then Hiccup realizes that he would be next and tries to compose himself again.

"Henry H. Haddock the third". Hiccup stands up and his gaze is drawn to the crowd of people sitting right in front of the podium. The only people clapping and cheering are Mr. and Mrs. Ingerman, Fishlegs parents. He walks up the steps to the podium and shakes the principal´s hand, as Michael had just done a few seconds earlier. "Congratulations Mr. Haddock" the principal says as he hands Hiccup the role of paper. He takes his diploma and gives him a weak smile before he turns around and walks back to his seat.

After another boring hour of name calling and a final speech from a teacher it is all over. Hiccup sighs. The moment that should have been one of the best memories of his High School career turned out to be a complete waste of time. Then, before anyone has the time bother him, he walks to one of the bathrooms nearby and changes into his normal clothes.

He folds the diploma neatly and puts it in his pocket. Then walks out of the bathroom and out of the stadium. He gets into his car and pulls out of the parking lot. He takes a final look at the place he had grown to hate over last few years and then finally makes his way home.

**OoOoO **

_Half an hour late – Hiccups home – Hiccups Pov_

I finally turn right into the street I live in. I look at my watch and see that it´s already 2:30 pm. As I pull up into the driveway to my house I see a sight I didn´t expect to see at all today. My father´s bright red Dodge Ram stands right in front of the garage. I turn my own car off and get out.

While walking up to the front door I pull out my keys and start searching for one for the front door. As I finally find it I put it in the keyhole and open the door.

After I had closed the door behind me I look around the corner into the living room. There, on the couches sits my dad with his notebook on his lap, frantically typing on the keyboard.

As I enter the room he looks up. "Already home? I thought you would be at school for at least two more hours. Why are you here so early?"

I can feel my face turn into a scowl as he speaks and by the time he is finished, my blood boils in anger. I shove my hand in my pocket and pull out the folded diploma. I throw it at him and spit: "I just graduated from High School. I take it you didn´t remember that little detail about your son´s life in the morning?"

Now it´s his turn to get angry and he stands up to yell at me but before he could even a single word out, I cut him off. "You know what? I don´t even want to know the answer. All you ever did was work for your stupid company in your stupid office all the time. I guess your son is just second priority after all those important things you have to do."

By the time I finish my father´s face is red in anger and he starts shouting at me: "Henry Horrendous Haddock the third! Don´t you dare speaking to me like that! I work hard so we can afford this lifestyle!", he gestures around the room, "All this is here because _I_ work for it all day! And one day _you_ will take over the family business! I expect you to show a little more respect for your ancestors!"

"BUD I DON´T WANT TO WAKE OVER THE FAMILY BUSINESS! DON´T YOU GET THAT INTO YOUR STUBBORN HEAD?!", I yell back.

"YOU WILL DO AS I TELL YOU, HENRY! MAYBE THEN I COULD BE PROUD OF YOU AGAIN!"

As soon as those words had left his mouth, I turn around and grab my keys from the sideboard beneath the door and rush out of the house and over to my car. As I pull out of the driveway again, I can feel tears stinging in my eyes. '_I have to get away from him.' _Is all I could think of now.

As I drive along the streets of Berk, I automatically take the turns that would lead me to my favorite place in town. The airport. I park my car at the fence at the end of the runway and get out. That is the place I come to if I have to think about something.

Now I have to think about something too. About, what I would do now. I couldn´t go back to my house as long as he is still there. I am not able to face him right now because although I´ve already known that he isn´t exactly proud of me, it is like a punch in the face, to hear him actually say it.

While I´m standing here, watching the planes start and land, I hear a loud roar of an engine and as I look up at the sky I see a F-22 Raptor, a majestic fighter plane, fly right over my head.

Then an idea pops into my head. I don´t want to take over the family business and to show my father once and for all that he couldn´t force to, I would do something I wanted to do since I was a little kid. I am going to join the United States Air Force.

**OoOoO**

**Sooo…here is the second chapter of Wingmen and Hiccup finally made his decided what to do with his future and we started with our main plot.  
>I hope you liked the chapter, because it was a spontaneous decision to write the complete chapter today.<br>Please review and tell me your opinion.**

**Also special thanks to grandprincessanastasiaromanov5, and the Guest (you know you are meant ;D) who encouraged me to go on with the story. **

**-TheTenggi**


	3. Ch1 Leaving

**Hey I´m back with a new chapter for you guys!  
>Thank you all so much for supporting this story. I would have never imagined that people would like what I write. So it really surprised me to see that so many people read this fic and like it. I can´t thank you all enough for that. It really makes me happy to erite this story for you and I will keep going until you don´t like it anymore (or I just don´t have time to write anymore)<br>So…here´s the third chapter.**

**Disclaimer: I do not own How to train your dragon in any way. All rights go to Cressida Cowell and Dreamworks. I just own my OC´.**

**OoOoO**

_**Chapter 1: Leaving**_

_Air Force recruiting office – 4:15 pm – Normal Pov_

Hiccup turns into the little parking lot behind the small building next to the airport. He gets out of his car and locks it, before slowly walking back to the front door of the office.

As pulls the door open and steps into the room, he is greeted by a tall man with black hair, dressed in green camo clothing.

"Hello, Sir! I´m Lieutenant Taylor. What can I do for you today?", he says as he looks up from the computer screen in front of him. Hiccup nervously steps closer to the man.

"Uh…umm…Hello…I´m Henry Haddock and I want to join the US Air Force."

"Very good. Do you have a high school diploma?", the Lieutenant asks.

"Yes…In fact I just got it today" Hiccup rubs the back of his neck nervously. He just remembers that he would need to have specific requirements to join the Air Force. Although he isn´t worried about his intellectual abilities, he gets kind of nervous when he thinks about the physical requirements he would need.

"Great!" the man behind the desk exclaims enthusiastically, "Do you have it with you?"

"Uh…No"

"Well than I suggest you get it and come back then. And also bring your ASVAB score if you have already taken the test. I´ll wait here for you." Hiccup nods and then leaves the office again, making his way to the car parked behind the building.

As he is on the way home, he begins to worry even more, if he would be able to pass the physical medical exam. As he pulls into the driveway of his home, he notices, that his dad´s car is gone. _'Great! At least I don´t have to put up with him again' _he thinks, as he gets out of the car and walks to the front door.

After opening it, he hurries up the stairs and into his room. There he searches for his ASVAB score. As he finally finds the piece of paper, he walks back down the stairs and into the living room. There, on the couch, right where his father had been sitting, lays his diploma. He picks it up and puts in his pocket.

Then he walks out to his car again, gets in and drives back to the office building.

**OoOoO**

_Hiccups house – one week later – 7:30 am – Hiccup´s Pov_

I wake up as my alarm clock goes off. Annoyed at the loud noise I turn around and hit the button that would stop the ringing. Unfortunately the button is broken, so the noise just keeps going on, annoying me even more, so without further ado I just take the stupid thing and slam it against the wall.

Finally the room is quiet again. I lie back in my pillows and start thinking about the day, I signed up for the air force. After I had returned to the office, I took the physical medical test. I was surprised myself, as I was told I had just slightly passed the exam. After that I had signed the contract and set the date for my departure to basic training.

As a matter of fact, that is today. So I get up, put on my regular clothes, and start backing my backpack for the travel to the air force base.

When I have everything I would need, I pick up my mobile phone and put it in the pocket of my trousers. I go downstairs and get myself a breakfast. As it got usual over the past week, I ignore my father´s note on the kitchen table and enjoy my food.

As I finish eating, my phone vibrates in my pocket. I pull it out and see that it´s a message from Fishlegs.

_F: Hey Hiccup! I haven´t seen you since graduation…Is every alright?_

_H: Yeah…I just needed some time for myself to think about some stuff._

_F: Oh…Ok. If you need someone to talk to, you can just give me a call you know?_

_H: Yes I know Fish…_

_F: Come on Hiccup…Spit it out. What´s wrong? You usually would call me at least every third day to ask if I could hang out with you…_

_H: I don´t really want to talk about it._

_F: Oh come on…you know I can keep a secret!_

_H: *sigh* Ok…I joined the force after I had an argument with dad…_

_F: YOU DID _WHAT?! _Hiccup, you can´t be serious!_

_H: Well I am very serious._

_F: When did you plan on telling me this?_

_H: I…actually didn´t want to tell you at all._

_F: Shit, Hiccup…Why did you do this?_

_H: I don´t know…I guess I was just angry at dad. He tried to "talk" me into taking over the company again. I just have to show him that he can´t force me into this. And maybe he finally gets proud of me, when I can fly a fighter plane._

_F: You applied as pilot?! Couldn´t you have taken a less dangerous job like…an engineer or something?_

_H: No…You know I always liked airplanes, so if I join the air force, then I at least want get to fly a bit._

_F: I´m telling you, this is a stupid idea!_

_H: Well it´s too late to stop it anyways…I´ll go to basic training today._

_F: *sigh* I guess I can´t stop you then… Will you at least tell me, when you come back?_

_H: Well…Hehe …You know, the funny thing is I don´t really know when I will come back._

_F: Seriously? I just hope it´s soon then…_

_H: Yeah…Anyways, could you please keep it a secret? I don´t want my dad or anyone to know where I am…_

_F: Your dad doesn´t even know?!_

_H: No…So can you please keep my secret?_

_F: Ok Hiccup I will do as you ask me, but just under one condition: I want you to take me flying when you come back._

_H: Thank you, Fish! Of course I will take you flying…_

_F: Ok Hiccup…Good luck then and take care of yourself…_

_H: I will…bye._

_F: Good bye, Hiccup_

With that I put my phone back in my pocket and get up from the table. Just then I hear the doorbell ring. I walk out of the kitchen and over to the front door. Cautiously I open the door and peer outside.

A man with dark brown hair, dressed like Lieutenant Taylor from the recruitment office, stands right in front of the door, looking impatiently at his watch. As I open the door he looks up and frowns.

"Henry Haddock?", he asks.

"That´s me."

"Good", his expression lightens a little bit, "Are you ready to go?"

"Yeah…Just let me get my backpack and I´ll be right there." He nods and I hurry back in the kitchen and grab my belongings. Then I walk back to the door and step outside.

I close the door behind me and follow the man to a dark green truck, parked on the opposite side of the street. As I wait for a car to pass by, I take one look back at my home. I know I won´t see it for a long time.

I turn around and walk across the street. The man with the brown hair gestures for me to climb in at the back of the truck. After I had pulled myself up, I look at the rows of seats on both sides of the truck. On my left is a guy with pitch black hair and bright green eyes. He looks at me curiously. The right row is completely empty, so I take a seat opposite of the only other passenger.

I can hear a door close and shortly after, the truck´s engine roars up and we drive down the street I´ve lived in for all my life.

The other guy is still looking at me and it would be a long journey to the base, so I decide to try and make a friend.

"Hey…I´m Henry", I say and extend my hand. "Timothy, but no one ever calls me that…" he answers and takes my hand to shake it.

Confused by his words I look at him. "So... what do they call you then?"

He looks down, a little blush on his cheeks, as if I had asked him something embarrassing. But well, considering my own nickname I guess I would be embarrassed too.

"Toothless…", he finally says in a small voice. "They call you Toothless?! Why is that?"

"Uhm…You know…when I was in elementary, I had a pet snake…and it had no teeth. So after my friends found out, they somehow came up with calling me Toothless and it kind of stuck."

"Hm…Well my nickname is Hiccup, so…"

"Hiccup?! Are you kidding me?", he looks as if he is about to burst out laughing. Now it is my turn to get embarrassed and I feel a strange urge to jump right back out of the vehicle.

"No…I´m serious. I´m called Hiccup.", I say, "My cousin came up with it, ´cause when I was younger I would constantly get Hiccups…"

Toothless chuckles a little at that and then asks: "Soo… Hiccup, tell me, why did you join the air force?"

"Well…mainly because of my dad. He would always push me to take over the family business, which I absolutely despise." I don´t know why, but it feels really good to talk to someone else than Fishlegs about my father. "And why did you, Toothless?", I ask, using the nickname, just like him.

"Well…I´m an orphan you know? So as soon as I got my high school diploma, I ran up to the recruitment office. I just couldn´t put up with all those annoying people anymore and, considering I always loved flying, the air force seemed like a good place to go."

"I see…So you didn´t want to go back to the orphanage?"

"No…I absolutely hate that place, with all the rules and all the annoying keepers..."

I hear the squeaking of the breaks, the truck slows down and comes to a stop. Then the door on the driver´s side is yanked open and slams against the side of the truck with a loud metallic noise.

We both stop speaking, as we eavesdrop on the conversation, the driver has with, what sounds like a very proud father:

"…my boy. Of course he joined the air force. I would be disappointed if he hadn´t! Just like me all those years ago!", a booming voice, not unlike my fathers, just filled with pride, calls out.

Shortly after we hear the shutting of a wooden door and footsteps are heard coming to the back of the truck. "Now get in there boy." We hear the driver´s voice from outside. A second later a head appears above the edge, as young man about my age pulls himself up.

Just like me, he has a small backpack over his shoulder and looks at his surroundings. He has dark hair and a small goatee. As he notices us, he clears his throat and takes sits down beside me.

"Hey…", he said. "Hi", Toothless and I say in unison.

"Ahm…I´m Thomas…", he says.

"I´m Henry, he is Timothy. But you can call us Hiccup", I gesture to me, "and Toothless", I point at the boy opposite of us.

"Ok…Well my nickname is Thuggory so… I guess you can call me that.", he grins and without before I could even think about it I grin back. For the first time in my almost nineteen year old life, I feel like I really have friends. You might think it´s pathetic… I guess you´re right with that. But… the good thing is… I don´t care at all. All I know is that I might have more than one friend now and that really makes me happy. I know that the rest of the drive to the air force base wouldn´t be as boring as I thought after all.

**OoOoO**

**Yeah… That was the first actual chapter…  
>So… Hiccup met Toothless and Thuggory now. Next time the group will arrive at the air force base…<strong>

**I apologize for being inaccurate with writing the whole talking with the recruiter, but I don´t really have the energy to write this whole procedure… Also I know that the requirements to become an air force pilot are way more than just the little exams and grades I´ve mentioned in this chapter but I couldn´t write about all the requirements because they were confusing me or just not writable, if I want to get Hiccup into the cockpit really fast (which I definitely want). So if any of think I should have written it all, I apologize for not doing so.  
><strong> 

**Anyways I hope you enjoyed it this chapter and as always, feel free to leave a review, ´cause I want to what exactly you think about this story.  
>Also a great "Thank you!" to all the people who favored, followed and reviewed thus far. Thank you all so much, you´re the greatest of all! ;D<strong>

**-TheTenggi**


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